Annie Croner:
Welcome to The Whole Assistant Podcast where assistants come to embrace their badassery and discover how to show up more strategically for their careers, their executives, and most importantly, themselves. I'm your coach, Annie Croner. Join us as we dive into the skills, strategies and mindset that will help you unleash your full potential. Let's go. Welcome back to the Whole Assistant Podcast. Today I'm going to be talking about a situation that many of us have found ourselves in. And I know that many of us have found ourselves in this situation because I've come across so many people recently who are dealing with this scenario. And that scenario is dealing with an executive who's never had an executive assistant before.
Annie Croner:
Maybe they're a first time founder, maybe they are a person who works their way up to the ranks and are gifted you and they don't know how to leverage you, they don't know how to utilize you. How do we handle that situation? And I was recently on a call for Leveled up, which is my group training and coaching program and this cohort. There are a lot of people who are dealing with this situation where they are dealing with a leader who has never worked with an executive assistant before. And so on this specific call, that's all that showed up. Or four people who were working for an executive, they never dealt with an executive assistant before and they were discussing some of the challenges. This was our first coaching call in this cohort and I just thought I'd hop on here and share my best strategies for dealing with this situation. So first of all, there are a couple different scenarios when it comes to dealing with an executive who has never had support before. The first is there again.
Annie Croner:
They work their way up through the ranks and are gifted another human being. Here you go. O.C. suite executive for the first time, you now have this person at your disposal and. And they don't know what to do with you because they've literally gotten to where they are because of their resourcefulness, their resilience, their ability to fend for themselves, all the things. And so that can be challenging. Another scenario is you're dealing with a first time founder who not only do they not know how to utilize you, this is their baby. This is the first time they have started a company perhaps and they don't want to relinquish control.
Annie Croner:
They love their business and that can also be super challenging. And both of these scenarios are going to require patience, they're going to require leadership on your part in terms of how you lead your leader and that sort of thing. They are also going to require you to educate your leader on how to best leverage you. And for a lot of us this is going to be an uphill battle because there again self sufficienc, resourcefulness, leaning on their own wisdom has gotten them to this place in life where they are now experiencing some level of success. So how do you actually leverage this whole other person that you have at your disposal? And there are some common barriers to success that I have noticed when it comes to managing a leader who has never worked with an executive assistant before. And the first category of barriers are control related barriers, things like not wanting to relinquish control so of your inbox perhaps, or perhaps interactions with other people or even relinquishing control in terms of your calendar management, that sort of thing. It can be incredibly challenging to our leaders who give us access to things. And I see this as very common, especially with new time leaders giving access to the inbox.
Annie Croner:
And what will happen is the executive assistant, especially if they are seasoned executive assistant will be talking with their leader, will be like, hey, I need access to your inbox just so I keep an extra set of eyes, just so I can know some context for some of the meetings that you want to set up. And the leader will say no, okay. And what ends up happening is we retreat. We don't actually use our voice from then on. We don't advocate for ourselves anymore. Instead of viewing the situation from the vantage point of planting a seed, which I'm going to talk about planting seeds here in a minute. But we definitely want to make sure that we aren't retreating, that we are, are maybe relenting here. We lost the battle.
Annie Croner:
But there are scenarios in which you can bring this up again. So say something gets missed on a calendar invite because your executive didn't forward you the email chain or whatever just asked you to maybe verbally schedule a meeting with someone and you didn't have the whole context of the meeting and something got lost in translation with a meeting invite. That is a good example of where you could bring up having access to their inbox so you have fuller context with regards to these meetings. So yes, it's a no in the moment. It may not be a no for forever. And I'm not saying we want to be pushy, but there are situations that we can point out or circumstances that we can point out where it would have been beneficial to have access to their inbox. Another common barrier to success around the control piece is micromanagement. And it's really interesting now being a business owner myself, and I've got two people working underneath me.
Annie Croner:
I've got a community manager and then I just hired a head of content. And it is a real challenge for me to relinquish control a lot of the time, especially around the content piece, because I am very particular with verbiage, I am very particular with the words I use, I am very particular with what I put out to you all. And I'm very intentional with those things because I know my audience, I know you all so well, and I've just had a real challenging time letting go some of those things. And I see that in myself. And because I also worked as an executive assistant for 20 years, I also understand the ins and outs of all of that. And I also know I can't micromanage my people. And I also know that 80% done my way is 100% awesome. So I've got a book recommendation for your executive.
Annie Croner:
If your executive has a hard time relinquishing control and they are a bit micromanagy, Dan Martell's book Buy Back youk Time will be beneficial for them. So it's Buy Back youk Time by Dan Martell. I will link to it in the show notes below. I will say that Dan's book has a pretty surface level understanding of the executive assistant role like most executives do, but he is really good about advocating for relinquishing control of certain things you're hiring someone to do. You're literally bringing people on board to surround you, people who are smart, people who have different vantage points, and you are tasking them with running different parts of your company, running different initiatives, that sort of thing. If you are not actually relinquishing control, it's going to be problematic. And as an executive assistant who may be supporting someone like this, I'm sure you understand this. So there again, we want to step into the role of guide.
Annie Croner:
We want to, we want to remind our executives that they have in fact hired people who are equally as smart, if not smarter than them in certain areas and to relinquish that control piece. Another kind of common thing when we're dealing with an executive who's never had support before is perfectionism, this idea that we want people to do things our way 100 of the time. And I'm going to reference Dan Martel's book again. We want to make sure that we recognize that people are going to do things differently than we do. And this is where really stepping into that role of guide, which I broke down in last week's episode go. So go have a listen to that episode where I talk about stepping out of the role of rescuer as an executive assistant and really embodying the role of guide can be super beneficial when it comes to coaching our executives. In a way, managing up, especially if you are a seasoned executive assistant and your executive is not really used to having an executive assistant alongside them, you are going to be the one with the knowledge and understanding here. Okay? Now there are also awareness barriers to success and those are things like lack of trust and look, trust.
Annie Croner:
I'm going to break down what trust looks like in just a minute. But actually developing trust and cultivating trust and making sure that you're showing up in a trustworthy way can go a long way in breaking down that barrier. And then also lack of maturity. Honestly, I've dealt with so many executive assistants at this point. I've clocked thousands of hours of coaching executive assistance and occasionally we'll come across somebody where the executive is just being immature. There's just a lack of maturity on their part. They don't have any understanding of how normal workings and businesses go. They've not been at a high level before and they're just kind of not grasping some of the core concepts around showing up mature and around what the expectations should be.
Annie Croner:
More often than not, that's really what it comes down to is like the expectations are so over the top, then nobody could meet the standard. And that is due to a lack of maturity a lot of times in the leader and and then lack of understanding of how to leverage an assistant. Of course. And I think a lot of executives don't understand how to leverage an assistant. But if this is particularly true, if you've never had an assistant before, a lot of people think that it's just your job to go get me coffee. It's going to be your job to manage my calendar. It's going to be your job to book my travel or to do my expense reports. Yes.
Annie Croner:
And there's so many other ways to leverage your support professional. There are so many other strategic partnership tactics that you could implement that could be really instrumental in your success as an executive. And so making sure that you guys know these things and that these are common things that I see, I hope will help level set for you that you are not the only one dealing with this situation, that you're not the only one dealing with this type of tricky executive, especially if your executive has never had a support person before. Now I'm going to share briefly some strategies to keep you in your power and to manage up professionally and to make sure that we're staying in our own lane emotionally. Because dealing with these situations can be super challenging and it can be really off putting when we're dealing with someone who isn't taking our ideas. We're dealing with someone where maybe we set up a system and they aren't listening to us. All of those things can be super challenging. So there again, my first strategy for you is to step into the role of guide.
Annie Croner:
We want to get out of this idea of trying to save our executive from something. There is nothing to save your executive from. And step into the role of guide because you, your executive is going to have to make mistakes, especially if they are a newer executive, especially if they are new to having a support person, especially if they don't have as much experience under their belt, they are going to make a lot of mistakes. And what I see happen more often than not is that we step into this role of rescuer and we're trying to like go around and cushion the blows for our executive and do all the things to try and save him from himself or save her from herself. We don't want to do that. We want to allow for the broad range of human emotion to come up in our executives. We want to allow for that learning experience to happen. Otherwise those lessons won't be learned and you're actually stunting their growth as well.
Annie Croner:
So there again, step into the role of guide. Go listen to last week's episode where I talk about releasing the role of rescuer and really embodying the empowerment and the role of guide. It will go a long way in helping you in this conversation as we talk about really managing a newer executive or an executive who's never had a support professional by their side before. Okay, the second thing we want to do is we want to educate as a part of that rule of guide. We're going to educate on what we are capable of, what we have handled in the past for former employers, what we feel like we could perhaps leverage or holes that we're seeing or that sort of thing. And I will also say that sometimes we just do. If you've developed a relationship with your executive and if you have trust, that's the important thing here. If you actually have established trust with your executive and you're dealing with a newer executive, you can totally take the step and do the thing.
Annie Croner:
And if you miss the mark, you can ask for forgiveness later. And I think that oftentimes leaders get really bogged down by the weight of decision making. And so anything you can do to lighten that load and make the decision, so long as you've established trust, that is key if you're going to be making decisions, especially if you are empowered to make those decisions, can go a long way in reducing mental fatigue for your executive. And decision fatigue, which is a very real thing. And I'm noticing this now on this side of the table where I am the boss and my own company. It's really fascinating to kind of watch because sometimes I'll just tell my people, like, just go make the decision. I don't care if it's wrong. I trust you.
Annie Croner:
Just go make the decision and then I will give you feedback. And sometimes also, I don't know what I want until I see something. And I know I, I know what I don't want. So until something is put out there, I'm not sure how I can make it better. And so this is particularly true when it comes to the content creation piece. And I there again, I, I just hired a new head of content for my business and we just went over a batch of content earlier this week and I was talking about different verbiage I like to use and stuff like that, but I didn't know what I wanted, I didn't know what I wanted to post or how I could potentially repurpose my content to go on social media. I had no idea. And so reducing that decision fatigue and hiring that person, having that person make decisions for me, and then me reviewing and being like, oh, okay, this, these are the tweaks I would make.
Annie Croner:
But sometimes we don't know what we want until we're presented with something. So go make the choice, make the decision, put it out there and then get your executives feedback, maybe on the back end or take the step you know you need to take and ask for forgiveness later. If you have developed that relationship with your executive, if you have developed that trust, do not do this unless you've developed that trust piece. But definitely, as much as you can reduce the decision fatigue, it will go a long way. And then secondly, we also want to cultivate trust. So I was talking about trust when I was talking about a barrier to success and how lack of trust can be a total barrier to success. We cultivate trust several ways. We cultivate trust by showing up consistently.
Annie Croner:
So you're sitting at your DEs. When you say you're going to be there, you do what you say you're going to do. When you say you're going to do it, you don't show up late, you show up consistently with integrity, on time, again and again and again. That cultivates trust. Another strategy for cultivating trust is communication. And I think everybody is guilty of this. Our executives are going to be guilty of this, especially because they're new and working with you. They don't know how best to communicate with you.
Annie Croner:
And so figuring out that communication piece with your executive is going to be paramount to your success. And in my last role, I thought my executive was going to be totally on board with having access to my Trello board. So I set him up with this app on his phone. I did all the things. I gave him access to my Trello board. It was not his communication style, nor did he want to have weekly touch bases or daily touch bases. What ended up working for us was a weekly update email. I had a template for the email that was outlined in terms of buckets of work.
Annie Croner:
And then at the very end of that email, I had things I needed from him and my plan for the upcoming week. And that communication style worked really well for us. So part of this is going to be trial and error, especially if your executive has never had a support person before. You're going to have to try a few different things until you figure out what sticks with them, until you figure out what lands in order for you to get what you need to do your job. I also recognized in my last role that my executive really did not mind texting. And so I'd send him a text if something was urgent, and I also told him to send me a text if something was urgent because I didn't want to live in my inbox. So figuring out that communication style will also help to cultivate trust. And then once you have that communication style in place, actually sticking with the plan, actually being overly communicative, letting him know or them know what it is you have on your plate, what you're executing on, what it's, what it is that you plan to work on the following week.
Annie Croner:
All of those things can be huge when it comes to building trust. And I think also our executives have no idea how we spend and utilize our time. So we also need to be articulating our value proposition, and we need an avenue by which to do that. So in your daily touch base, weekly touch base, letting your executive know what has been executed on and what you have saved them from in terms of things landing on their plate can also go a long way in establishing trust as well. Third kind of thing to establish trust is transparency. We need to be transparent with what's on our plate. We need to be transparent with our skill set. We need to be transparent with all of those things.
Annie Croner:
Otherwise our executive may not know how to guide us. Or you may let something fall through the cracks because we aren't quite sure how to execute. Right. We don't want that to happen. And then, of course, integrity is also going to be paramount to success. Letting your executive know when you made a mistake, and that mistake can actually serve to foster trust and not tear it down. If we actually take ownership, if we actually show up with integrity and radical accountability. And then, last but not least, time.
Annie Croner:
Sometimes it just takes time to establish trust. And, and I'll ask executive assistants, especially if they're noticing something off with the trust in their relationship. I will ask them, how long have you been working with this executive? And they'll say something like, oh, three weeks, a month, two months, three months. I'm like, well, no kidding, you've not established trust yet. Trust is built by doing all of these things over time, by showing up consistently, having good communication, being transparent, showing up with integrity over time, that's what builds trust. And then also another kind of strategy to keep you in your power is just to recognize that your brain works differently than theirs. Okay, so many executive assistants are very forward thinking. We are seeing problems long before those problems land on our executive's radar.
Annie Croner:
And this can feel really off putting when we bring up something and it gets shot down, or we bring up a solution to a problem that hasn't happened yet, but we're seeing it, we're seeing it coming, and it's ignored or dismissed or disregarded. And what's really fascinating about this piece is that more often than not, the executive will circle back a few weeks later, a month later, two months later, and they'll be like, hey, I just had this really great idea. And you're sitting there going, yes, I know, I had that idea two months ago. What is happening right now? And it can feel like you're being gaslit, but I will say that that's not actually what's going on. What's going on is that you planted a seed and that seed took root and it grew. And I understand this feeling of frustration, I do, because I had been there before. I've been to the place where I have presented something, it's got shot down, and then two months later, it was my exec's brilliant idea. Here's the deal, though, at least they're acting on it now.
Annie Croner:
And I, as someone who is now running her own company and sees and understands these things. I have a fuller perspective because now I'm on this side, which is just kind of really meta and weird for me, to be perfectly honest, because for so long I was on the side of the executive support person and I have so much going on in my brain at any given point in time, any given moment. And my guess is that your leader does as well. So show them grace. Still be forward thinking, still point out issues, still point out potential problems, still point out things that are coming down the pike that you see that they may not know about or be aware of, but also take into account that they may not act as fast as you would have them act, or they may not onboard an idea as soon as you would have them onboard it. But every time you bring it up, you are planting that seed or you are watering that seed. So that is what I have for you guys today. I hope you found this episode helpful and I just wanted to name that Working with an executive who has never had a support professional can be very challenging.
Annie Croner:
It can also be super rewarding depending on the type of person that you're dealing with, depending on whether or not they're an actually good person or how much training you're going to have to do to get them on board with your plans or to get them on board with best practices. But there again, I would have you rely on your own enoughness in the space of working with a new executive. Recognize that it is them, not you, most of the time. And then we adapt accordingly, like we do for many things in this role. Right? We're going to adapt. We're going to continue to plant and water those seeds. We're going to continue to put best practices out there. We're going to continue to showcase our strengths and how we can level up and support them.
Annie Croner:
We're also going to continue to showcase our value. And we're going to do that from a place of enoughness, not from a place of trying to prove anything. All right, guys, that is what I have for you guys today. Be intentional. Be whole. That is all for now. Hey, before you go, don't forget to grab my free Strategic Planning Session guide. This stealthy playbook will help you and your executive find clarity on their priorities so you can make a greater impact.
Annie Croner:
Go to wholeassistant.com/guide or click the link in the Show Notes to snag your copy. And if you're loving the podcast, please subscribe, leave a review and share with another assistant Ready to level up. Thanks for listening and until next time, keep embracing your badassery.
